CA2145305A1 - A recycling process for the production of adipic acid and other aliphatic dibasic acids - Google Patents
A recycling process for the production of adipic acid and other aliphatic dibasic acidsInfo
- Publication number
- CA2145305A1 CA2145305A1 CA002145305A CA2145305A CA2145305A1 CA 2145305 A1 CA2145305 A1 CA 2145305A1 CA 002145305 A CA002145305 A CA 002145305A CA 2145305 A CA2145305 A CA 2145305A CA 2145305 A1 CA2145305 A1 CA 2145305A1
- Authority
- CA
- Canada
- Prior art keywords
- oxidation
- acid
- cyclohexane
- adipic acid
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002253 acid Substances 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 66
- 230000008569 process Effects 0.000 title claims abstract description 48
- 238000004064 recycling Methods 0.000 title claims abstract description 36
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 29
- 150000007513 acids Chemical class 0.000 title claims abstract description 28
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 228
- 239000001361 adipic acid Substances 0.000 title claims description 115
- 235000011037 adipic acid Nutrition 0.000 title claims description 114
- 238000004519 manufacturing process Methods 0.000 title description 23
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 172
- 239000003054 catalyst Substances 0.000 claims abstract description 52
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000001301 oxygen Substances 0.000 claims abstract description 42
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 42
- 239000011541 reaction mixture Substances 0.000 claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 38
- 239000007791 liquid phase Substances 0.000 claims abstract description 24
- 239000000543 intermediate Substances 0.000 claims abstract description 20
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- 239000007789 gas Substances 0.000 claims abstract description 17
- 230000001590 oxidative effect Effects 0.000 claims abstract description 15
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 15
- 150000007524 organic acids Chemical class 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 96
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 95
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 31
- 238000001816 cooling Methods 0.000 claims description 14
- 238000002955 isolation Methods 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 229910001882 dioxygen Inorganic materials 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 230000036961 partial effect Effects 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 150000001868 cobalt Chemical class 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 4
- 230000036647 reaction Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 153
- 239000012071 phase Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000011084 recovery Methods 0.000 description 26
- 150000001924 cycloalkanes Chemical class 0.000 description 23
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 20
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical group 0.000 description 13
- 235000011044 succinic acid Nutrition 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 10
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 229910000619 316 stainless steel Inorganic materials 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
- 230000006698 induction Effects 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000002311 glutaric acids Chemical class 0.000 description 7
- 239000001384 succinic acid Substances 0.000 description 7
- 150000003444 succinic acids Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 6
- -1 cyclic alcohols Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 4
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001279 adipic acids Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001722 carbon compounds Chemical class 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 229940011182 cobalt acetate Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical class C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
- 239000004914 cyclooctane Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 238000009283 thermal hydrolysis Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- JYYQHHRSFZMKIN-UHFFFAOYSA-N acetic acid;cyclohexane Chemical compound CC(O)=O.C1CCCCC1 JYYQHHRSFZMKIN-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000013139 quantization Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95163692A | 1992-09-25 | 1992-09-25 | |
| US07/951,636 | 1992-09-25 | ||
| US5378893A | 1993-04-26 | 1993-04-26 | |
| US08/053,788 | 1993-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2145305A1 true CA2145305A1 (en) | 1994-04-14 |
Family
ID=26732244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002145305A Abandoned CA2145305A1 (en) | 1992-09-25 | 1993-09-13 | A recycling process for the production of adipic acid and other aliphatic dibasic acids |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5463119A (en, 2012) |
| EP (1) | EP0662943A1 (en, 2012) |
| JP (1) | JPH08502473A (en, 2012) |
| CN (1) | CN1086803A (en, 2012) |
| AU (1) | AU4959993A (en, 2012) |
| CA (1) | CA2145305A1 (en, 2012) |
| MX (1) | MX9305629A (en, 2012) |
| TW (1) | TW238299B (en, 2012) |
| WO (1) | WO1994007834A1 (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2722783B1 (fr) * | 1994-07-21 | 1996-08-30 | Rhone Poulenc Chimie | Procede de preparation d'acide adipique par oxydattion directe du cyclohexane et recyclage du catalyseur |
| US5505920A (en) * | 1994-10-04 | 1996-04-09 | Bayer Aktiengesellschaft | Process for treatment of waste gas from a cyclohexane oxidation reactor |
| US5883292A (en) * | 1996-01-17 | 1999-03-16 | Twenty-First Century Research Corporation | Reaction control by regulating internal condensation inside a reactor |
| US5654475A (en) * | 1996-03-25 | 1997-08-05 | Twenty-First Century Research Corporation | Methods of making intermediate oxidation products by controlling oxidation rates in an atomized liquid |
| US6288270B1 (en) | 1996-06-24 | 2001-09-11 | Rpc Inc. | Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments |
| US6039902A (en) * | 1996-06-24 | 2000-03-21 | Rpc Inc. | Methods of recycling catalyst in oxidations of hydrocarbons |
| US6143927A (en) * | 1996-06-24 | 2000-11-07 | Rpc Inc. | Methods for removing catalyst after oxidation of hydrocarbons |
| US5922908A (en) * | 1996-06-24 | 1999-07-13 | Twenty-First Century Research Corporation | Methods for preparing dibasic acids |
| US6337051B1 (en) * | 1996-06-24 | 2002-01-08 | Rpc Inc. | Device for detecting formation of a second liquid phase |
| US5801273A (en) | 1996-08-21 | 1998-09-01 | Twenty-First Century Research Corporation | Methods and devices for controlling the reaction rate of a hydrocarbon to an intermediate oxidation product by pressure drop adjustments |
| EP0923524A1 (en) | 1996-08-21 | 1999-06-23 | Twenty-First Century Research Corporation | Methods and devices for controlling the reaction by adjusting the oxidant consumption rate |
| US20010053864A1 (en) * | 1996-08-21 | 2001-12-20 | Decoster David C. | Devices for controlling the reaction rate and/or reactivity of hydrocarbon to an intermediate oxidation product by adjusting the oxidant consumption rate |
| US6103933A (en) * | 1996-11-07 | 2000-08-15 | Rpc Inc. | Methods for controlling the oxidation rate of a hydrocarbon by adjusting the ratio of the hydrocarbon to a rate-modulator |
| US5817868A (en) * | 1996-11-12 | 1998-10-06 | Twenty-First Century Research Corporation | Method and devices for controlling the oxidation of a hydrocarbon to an acid by regulating temperature/conversion relationship in multi-stage arrangements |
| FR2757155B1 (fr) * | 1996-12-12 | 1999-11-12 | Rhone Poulenc Fibres | Procede de traitement de melanges reactionnels issus de l'oxydation du cyclohexane |
| FR2757154B1 (fr) * | 1996-12-12 | 2000-01-14 | Rhone Poulenc Fibres | Procede de preparation de diacides a partir des eaux de lavage des produits d'oxydation du cyclohexane |
| US5824819A (en) * | 1996-12-18 | 1998-10-20 | Twenty-First Century Research Corporation | Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| US5929277A (en) * | 1997-09-19 | 1999-07-27 | Twenty-First Century Research Corporation | Methods of removing acetic acid from cyclohexane in the production of adipic acid |
| US5908589A (en) * | 1997-12-08 | 1999-06-01 | Twenty-First Century Research Corporation | Methods for separating catalyst from oxidation mixtures containing dibasic acids |
| EP1054856A1 (en) | 1998-02-09 | 2000-11-29 | RPC Inc. | Process for treating cobalt catalyst in oxidation mixtures of hydrocarbons to dibasic acids |
| JP2002503715A (ja) * | 1998-02-19 | 2002-02-05 | アールピーシー インコーポレイテッド | 酸化混合物から触媒を分離する方法およびデバイス |
| FR2775685B1 (fr) * | 1998-03-05 | 2000-12-29 | Rhone Poulenc Fibres | Procede de separation et de purification de l'acide adipique |
| US6433220B1 (en) | 1998-07-02 | 2002-08-13 | Rpc Inc. | Methods of extracting catalyst from a reaction mixture in the oxidation of cyclohexane to adipic acid |
| US6340420B1 (en) * | 1998-07-06 | 2002-01-22 | Rpc Inc. | Methods of treating the oxidation mixture of hydrocarbons to respective dibasic acids |
| FR2784099B1 (fr) * | 1998-09-14 | 2000-11-24 | Rhone Poulenc Fibres | Procede de separation et de purification de l'acide carboxylique issu de l'oxydation directe d'un hydrocarbure |
| TW460452B (en) * | 1998-09-14 | 2001-10-21 | Rhodia Fiber & Amp Resin Inter | Process for the crystallization of carboxylic acid and process for manufacturing crystalline carboxylic acid |
| KR20020003238A (ko) | 1999-04-20 | 2002-01-10 | 추후보정 | 촉매수용액에서 물과 시클로헥사논을 아세트산으로치환하는 방법 |
| US6235932B1 (en) | 1999-06-18 | 2001-05-22 | Chemintel (India) Private Ltd. | Process for preparation of adipic acid |
| KR20020037729A (ko) * | 1999-06-25 | 2002-05-22 | 케민텔 (인디아) 프라이비트 리미티드 | 아디핀산의 제조방법 |
| DE60110582T2 (de) * | 2000-05-15 | 2006-02-23 | Lonza S.P.A. | Verfahren zur herstellung von carbonsäuren |
| CN102757332B (zh) * | 2011-04-27 | 2015-07-01 | 中国石油化工集团公司 | 一种环己烷氧化产物的处理方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2223493A (en) * | 1938-07-12 | 1940-12-03 | Du Pont | Oxidation of cyclic compounds |
| US2589648A (en) * | 1950-05-26 | 1952-03-18 | Pan American Refining Corp | Cycloalkane oxidation |
| US3231608A (en) * | 1961-08-28 | 1966-01-25 | Gulf Research Development Co | Preparation of dibasic acids |
| US3390174A (en) * | 1964-06-17 | 1968-06-25 | Gulf Research Development Co | Process for the preparation of adipic acid |
| GB1115921A (en) * | 1964-12-21 | 1968-06-06 | Ici Ltd | The oxidation of saturated hydrocarbons |
| GB1304855A (en, 2012) * | 1969-08-05 | 1973-01-31 | ||
| US3657334A (en) * | 1969-12-04 | 1972-04-18 | Inst Francais Du Petrole | Process for producing adipic acid |
| US4032569A (en) * | 1975-07-14 | 1977-06-28 | Gulf Research & Development Company | Process for converting cyclohexane to adipic acid |
| US4158739A (en) * | 1978-03-20 | 1979-06-19 | Gulf Research & Development Company | Process for converting cyclopentane to glutaric acid |
| US4263453A (en) * | 1979-12-10 | 1981-04-21 | Gulf Research & Development Company | Process for converting cyclohexane to adipic acid |
| US5221800A (en) * | 1989-09-05 | 1993-06-22 | Amoco Corporation | One step air oxidation of cyclohexane to produce adipic acid |
-
1993
- 1993-09-09 TW TW082107379A patent/TW238299B/zh active
- 1993-09-13 WO PCT/EP1993/002471 patent/WO1994007834A1/en not_active Application Discontinuation
- 1993-09-13 EP EP93919326A patent/EP0662943A1/en not_active Ceased
- 1993-09-13 CA CA002145305A patent/CA2145305A1/en not_active Abandoned
- 1993-09-13 AU AU49599/93A patent/AU4959993A/en not_active Abandoned
- 1993-09-13 JP JP6508626A patent/JPH08502473A/ja active Pending
- 1993-09-14 MX MX9305629A patent/MX9305629A/es unknown
- 1993-09-25 CN CN93117985A patent/CN1086803A/zh active Pending
-
1994
- 1994-02-28 US US08/203,453 patent/US5463119A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1086803A (zh) | 1994-05-18 |
| EP0662943A1 (en) | 1995-07-19 |
| JPH08502473A (ja) | 1996-03-19 |
| TW238299B (en, 2012) | 1995-01-11 |
| AU4959993A (en) | 1994-04-26 |
| WO1994007834A1 (en) | 1994-04-14 |
| MX9305629A (es) | 1994-06-30 |
| US5463119A (en) | 1995-10-31 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |